Ethyl-Flurbiprofen
Flurbiprofen is a nonsteroidal antiinflammatory drug (NSAID) used in treatment of mild-to-moderate pain and symptoms of chronic arthritis. The kinetic resolution of (R,S)-flurbiprofen by enantioselective esterification with methanol or ethanol is of importance. The use of lipase immobilized on supports to obtain the optically pure enantiomers of chiral drugs in reactions carried out in organic solvents is a great challenge
General
Type : Not AlphaBeta Hydrolase target, Drug, Pro-Drug, Propionate, Alkyl ester
Chemical_Nomenclature : ethyl 2-(3-fluoro-4-phenylphenyl)propanoate
Canonical SMILES : CCOC(=O)C(C)C1=CC(=C(C=C1)C2=CC=CC=C2)F
InChI : InChI=1S\/C17H17FO2\/c1-3-20-17(19)12(2)14-9-10-15(16(18)11-14)13-7-5-4-6-8-13\/h4-12H,3H2,1-2H3
InChIKey : JIYXQCWLSQSIJV-UHFFFAOYSA-N
Other name(s) : Flurbiprofen Ethyl Ester || Ethyl Flurbiprofen || SCHEMBL9555720
MW : 272.31
Formula : C17H17FO2
CAS_number : 64858-90-8
PubChem : 10084622
UniChem : JIYXQCWLSQSIJV-UHFFFAOYSA-N
Target
Structures : No structure
Families : Hormone-sensitive_lipase_like, Bacterial_lip_FamI.3, Canar_LipB
References (9)
| Title : A New Approach in Lipase-Octyl-Agarose Biocatalysis of 2-Arylpropionic Acid Derivatives - Siodmiak_2024_Int.J.Mol.Sci_25_5084 |
| Author(s) : Siodmiak J , Duleba J , Kocot N , Mastalerz R , Haraldsson GG , Marszall MP , Siodmiak T |
| Ref : Int J Mol Sci , 25 : , 2024 |
| Abstract : |
| PubMedSearch : Siodmiak_2024_Int.J.Mol.Sci_25_5084 |
| PubMedID: 38791124 |
| Title : Enhanced Production of (S)-2-arylpropionic Acids by Protein Engineering and Whole-Cell Catalysis - Liu_2021_Front.Bioeng.Biotechnol_9_697677 |
| Author(s) : Liu X , Zhao M , Fan X , Fu Y |
| Ref : Front Bioeng Biotechnol , 9 :697677 , 2021 |
| Abstract : |
| PubMedSearch : Liu_2021_Front.Bioeng.Biotechnol_9_697677 |
| PubMedID: 34307324 |
| Gene_locus related to this paper: 9zzzz-Est924 |
| Title : Encapsulation of lipase using magnetic fluorescent calix[4]arene derivatives\; improvement of enzyme activity and stability - Ozyilmaz_2019_Int.J.Biol.Macromol_133_1042 |
| Author(s) : Ozyilmaz E , Cetinguney S , Yilmaz M |
| Ref : Int J Biol Macromol , 133 :1042 , 2019 |
| Abstract : |
| PubMedSearch : Ozyilmaz_2019_Int.J.Biol.Macromol_133_1042 |
| PubMedID: 31042560 |
| Title : Synthesis of L-Ascorbyl Flurbiprofenate by Lipase-Catalyzed Esterification and Transesterification Reactions - Xin_2017_Biomed.Res.Int_2017_5751262 |
| Author(s) : Xin JY , Sun LR , Chen SM , Wang Y , Xia CG |
| Ref : Biomed Res Int , 2017 :5751262 , 2017 |
| Abstract : |
| PubMedSearch : Xin_2017_Biomed.Res.Int_2017_5751262 |
| PubMedID: 28421196 |
| Title : Enantioselective resolution of racemic flurbiprofen methyl ester by lipase encapsulated mercapto calix[4]arenes capped Fe(3)O(4) nanoparticles - Yildiz_2017_Bioprocess.Biosyst.Eng_40_1189 |
| Author(s) : Yildiz H , Ozyilmaz E , Bhatti AA , Yilmaz M |
| Ref : Bioprocess Biosyst Eng , 40 :1189 , 2017 |
| Abstract : |
| PubMedSearch : Yildiz_2017_Bioprocess.Biosyst.Eng_40_1189 |
| PubMedID: 28488138 |
| Title : Direct enantioselective HPLC monitoring of lipase-catalyzed kinetic resolution of flurbiprofen - Ghanem_2010_Chirality_22_597 |
| Author(s) : Ghanem A |
| Ref : Chirality , 22 :597 , 2010 |
| Abstract : |
| PubMedSearch : Ghanem_2010_Chirality_22_597 |
| PubMedID: 19899153 |
| Title : R-stereopreference analysis of lipase Novozym 435 in kinetic resolution of flurbiprofen - Zhang_2007_Chirality_19_245 |
| Author(s) : Zhang HY , Wang X , Ching CB |
| Ref : Chirality , 19 :245 , 2007 |
| Abstract : |
| PubMedSearch : Zhang_2007_Chirality_19_245 |
| PubMedID: 17094073 |
| Title : Molecular cloning and functional expression of esf gene encoding enantioselective lipase from Serratia marcescens ES-2 for kinetic resolution of optically active (S)-flurbiprofen - Lee_2007_J.Microbiol.Biotechnol_17_74 |
| Author(s) : Lee KW , Bae HA , Lee YH |
| Ref : J Microbiol Biotechnol , 17 :74 , 2007 |
| Abstract : |
| PubMedSearch : Lee_2007_J.Microbiol.Biotechnol_17_74 |
| PubMedID: 18051356 |
| Gene_locus related to this paper: serma-lipasA |
| Title : Experimental optimization of enzymic kinetic resolution of racemic flurbiprofen - Zhang_2005_Biotechnol.Appl.Biochem_42_67 |
| Author(s) : Zhang HY , Wang X , Ching CB , Wu JC |
| Ref : Biotechnol Appl Biochem , 42 :67 , 2005 |
| Abstract : |
| PubMedSearch : Zhang_2005_Biotechnol.Appl.Biochem_42_67 |
| PubMedID: 15651979 |